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An ambitious contender for Nancy Pelosi’s congressional seat, often touting his connections with Alexandria Ocasio-Cortez, found himself in an awkward position recently. Despite his frequent promotions of their past association, the progressive stalwart refrained from backing him during a recent video interview.
While speaking to a reporter from Drop Site, Ocasio-Cortez was questioned about her views on Saikat Chakrabarti. Chakrabarti, who had a brief stint as her chief of staff following her 2018 congressional win, is now pursuing a seat in Congress representing San Francisco.
When asked about her former aide, Ocasio-Cortez artfully dodged the inquiry. “For me, overall, I’m trying to think about the role I’m trying to play more broadly in these things,” she commented, steering clear of a direct endorsement.
Chakrabarti, a wealthy progressive Democrat, has used his past association with the Bronx congresswoman as a central theme in his campaign materials and public statements. His efforts to leverage their prior professional relationship highlight the complex dynamics of political endorsements and alliances.
Chabrakarti, a multimillionaire lefty Democrat who was Ocasio-Cortez’s congressional aide for roughly six months before resigning, has prominently featured the Bronx congresswoman in campaign literature and talking points.
“Having worked with AOC, I can safely say she’s one of a kind. But I’d be honored to represent San Francisco in Congress and join AOC to build a society that truly works for all,” Chakrabarti boasted in an X post announcing his campaign last year.
Chakrabarti, 40, struck it rich working for financial tech firm Stripe and has plowed $5 million into his own campaign for retiring Rep. Nancy Pelosi’s seat.
The Harvard-educated tech multimillionaire describes himself as a former tech director with Sen. Bernie Sanders’ failed 2016 presidential bid and “the architect of the Green New Deal.”
He worked for Ocasio-Cortez’s 2018 campaign for Congress, when she defeated incumbent Rep. Joe Crowley in an upset.
Chakrabarti then joined the new congresswoman in the House of Representatives — where he quickly gained a difficult reputation after instigating nasty public spats with Democratic colleagues, according to media reports at the time.
Ocasio-Cortez went on to explain that she has a “lean” political staff in the Thursday interview.
“There are 435 seats in Congress, right? And there is this moment where it’s like — and not just in this race but any race, once you go in it’s like ‘what about this one, and this one?’” she said.
Chakrabarti is competing against state Sen. Scott Wiener, city Supervisor Connie Chan and Marie Hurabiell, a lawyer and activist.
The Texas native has racked up endorsements from drag performer Peaches Christ and former congressman Jamal Bowman, who lost his 2024 reelection bid after pulling a fire alarm at the Capitol, resulting in a $1000 fine.
Chakarabarti also raised eyebrows for gushing over the polarizing far-left streamer Hasan Piker, whose racist tirades calling Asian Americans “dogs for white people” came to light this month.
Chakrabarti did not respond to a request for comment.
Young Turks host Cenk Uygur, Chakrabarti’s pal who has attempted to brand him as a “West Coast Zohran Mamdani,” furiously denounced Ocasio-Cortez and demanded she endorse him in a video posted Friday.
“I can’t believe she hasn’t endorsed him yet,” he fumed.